A Cascade Reaction Consisting of Pictet−Spengler-Type Cyclization and Smiles Rearrangement: Application to the Synthesis of Novel Pyrrole-Fused Dihydropteridines

Abstract

[reaction: see text] Tandem Pictet-Spengler-type cyclization and Smiles rearrangement have been discovered in the synthesis of pyrimidine-fused heterocycles. The reaction of 4-chloro-5-pyrrol-1-ylpyrimidine amino aldehyde with an amine under an acidic condition yielded the Pictet-Spengler-type cyclization product diazepine, which readily underwent Smiles rearrangement to give a novel pyrrolo[1,2-f]pteridine derivative.